Tetrahydrofuran → HCID 86649454, compound

HRID 1510310Notes

Reaction equation

HRID 1510310 reaction equation
C([C:3]1[S:7][C:6]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=[C:12]([O:23][CH:24]([CH3:26])[CH3:25])[CH:11]=2)=[N:5][CH:4]=1)=O.[C:28]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:30][CH2:31][CH3:32])=[O:29].[CH2:53]1COCC1>>[CH2:31]([O:30][C:28](=[O:29])[CH:33]=[CH:53][C:3]1[S:7][C:6]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=[C:12]([O:23][CH:24]([CH3:25])[CH3:26])[CH:11]=2)=[N:5][CH:4]=1)[CH3:32]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86649453N-(5-Formylthiazol-2-yl)-3-isopropoxy-5-phenoxybenzamide

Product 1

HCID 86649454HCID 86649454, compoundYield 67%

Procedure

3-[2-(3-Isopropoxy-5-phenoxybenzoylamino)-thiazol-5-yl]-acrylic acid ethyl ester (102 mg, 67%) was prepared from N-(5-formylthiazol-2-yl)-3-isopropoxy-5-phenoxybenzamide (130 mg, 0.34 mmol) and (carboethoxymethylene)triphenylphospho-rane (150 mg, 0.43 mmol) by heating a THF solution (5.0 mL) of the reactants at 50° C. overnight. Molecular sieves (4A) were added to remove any water in the reaction.

Workup

  1. customto remove any water
  2. customin the reaction

Sources & evidence

ORD record
ord-5ac9e02e72a342d2b9035e65ada14bfe
Source dataset
uspto-grants-2012_07
Patent number
US08211925B2

Reaction notes

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